Regioselective N-Methylation of 6-Chloroindolo[3,2-c]quinolines and Their Amination Reactivity at the C-6 Position

Regioselective N-Methylation of 6-Chloroindolo[3,2-c]quinolines and Their Amination Reactivity at the C-6 Position

The treatment of 6-chloroindolo[3,2-c]quinoline 6 with NaH–MeI led to methylation at N-11, forming 8, while the reaction of 6 with MeI with heating gave the corresponding 5-methylated quinolinium salt whose SNAr with water smoothly proceeded to form 5-methylindolo[3,2-c]quinolin-6-one 3b. The aminat...

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Veröffentlicht in:Bulletin of the Chemical Society of Japan 2013-07, Vol.86 (7), p.864-869
Hauptverfasser: Wang, Ning, Imai, Kento, Pang, Cui-Qing, Wang, Ming-qi, Yonezawa, Mizuho, Zhang, Yu, Nokami, Junzo, Inokuchi, Tsutomu
Format: Artikel
Sprache:eng
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Zusammenfassung:The treatment of 6-chloroindolo[3,2-c]quinoline 6 with NaH–MeI led to methylation at N-11, forming 8, while the reaction of 6 with MeI with heating gave the corresponding 5-methylated quinolinium salt whose SNAr with water smoothly proceeded to form 5-methylindolo[3,2-c]quinolin-6-one 3b. The amination reactivity at the C-6 was assigned in the order of 6 > 11-methylated 8.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20130063